5-{[4-(4-Bromo­phen­yl)thia­zol-2-yl]amino­methyl­ene}-2,2-dimethyl-1,3-dioxane-4,6-dione

In the title compound, C₁₆H₁₃BrN₂O₄S, the 1,3-dioxane-4,6-dione ring exhibits an envelope conformation. The amino H atom makes an intra­molecular contact to a carbonyl O atom, forming a six-membered ring.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.088
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  S1      ..       3.33 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O4      ..       3.35 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-{[4-(4-Bromophenyl)thiazol-2-yl]aminomethylene}-2,2-dimethyl-1,3- dioxane-4,6-dione

Crystal data

C16H13BrN2O4S	Z = 2
Mr = 409.25	F(000) = 412
Triclinic, P1	Dx = 1.685 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.8262 (6) Å	Cell parameters from 25 reflections
b = 9.4869 (7) Å	θ = 5.0–22.8°
c = 11.8847 (7) Å	µ = 4.90 mm^−1
α = 70.969 (5)°	T = 299 K
β = 79.213 (6)°	Thick needle, yellow
γ = 77.059 (6)°	0.60 × 0.25 × 0.15 mm
V = 806.72 (10) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2603 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 66.9°, θmin = 4.0°
ω/2θ scans	h = −9→1
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.198, Tmax = 0.479	l = −14→13
3288 measured reflections	3 standard reflections every 120 min
2774 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.4106P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.003
2774 reflections	Δρmax = 0.53 e Å^−3
218 parameters	Δρmin = −0.60 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0133 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0835 (3)	0.3092 (3)	0.4790 (2)	0.0358 (5)
C2	−0.2798 (3)	0.5084 (3)	0.5447 (2)	0.0394 (5)
H2	−0.3613	0.5912	0.5576	0.047*
C3	−0.1846 (3)	0.4042 (2)	0.6289 (2)	0.0343 (5)
C4	−0.1915 (3)	0.4066 (3)	0.7527 (2)	0.0352 (5)
C5	−0.1077 (3)	0.2839 (3)	0.8382 (2)	0.0398 (5)
H5	−0.0461	0.1989	0.8165	0.048*
C6	−0.1147 (3)	0.2870 (3)	0.9542 (2)	0.0432 (6)
H6	−0.0582	0.2050	1.0104	0.052*
C7	−0.2072 (3)	0.4137 (3)	0.9855 (2)	0.0413 (5)
C8	−0.2916 (4)	0.5364 (3)	0.9038 (2)	0.0491 (6)
H8	−0.3536	0.6207	0.9265	0.059*
C9	−0.2827 (4)	0.5327 (3)	0.7879 (2)	0.0462 (6)
H9	−0.3386	0.6157	0.7321	0.055*
C10	0.1531 (3)	0.1087 (3)	0.4488 (2)	0.0366 (5)
H10	0.1805	0.0916	0.5255	0.044*
C11	0.2563 (3)	0.0217 (3)	0.3809 (2)	0.0363 (5)
C12	0.3972 (3)	−0.0978 (3)	0.4330 (2)	0.0380 (5)
C13	0.5184 (3)	−0.0839 (3)	0.2285 (2)	0.0443 (6)
C14	0.2200 (3)	0.0405 (3)	0.2607 (2)	0.0422 (6)
C15	0.6043 (4)	−0.1992 (4)	0.1634 (3)	0.0596 (8)
H15A	0.7216	−0.2412	0.1845	0.072*
H15B	0.6101	−0.1512	0.0784	0.072*
H15C	0.5360	−0.2787	0.1857	0.072*
C16	0.6151 (4)	0.0458 (4)	0.2005 (3)	0.0600 (7)
H16A	0.6214	0.0982	0.1162	0.072*
H16B	0.7324	0.0078	0.2225	0.072*
H16C	0.5533	0.1143	0.2449	0.072*
Br1	−0.22471 (4)	0.42077 (4)	1.14469 (2)	0.06033 (16)
N1	−0.0720 (3)	0.2885 (2)	0.59049 (17)	0.0362 (4)
N2	0.0161 (3)	0.2160 (2)	0.41215 (18)	0.0399 (5)
H2N	−0.0128	0.2286	0.3427	0.048*
O1	0.5090 (2)	−0.16439 (18)	0.35441 (16)	0.0447 (4)
O2	0.3430 (2)	−0.0318 (2)	0.19316 (16)	0.0475 (4)
O3	0.4173 (3)	−0.1465 (2)	0.53740 (16)	0.0490 (4)
O4	0.0858 (3)	0.1120 (3)	0.21890 (19)	0.0632 (6)
S1	−0.22965 (8)	0.46702 (7)	0.41146 (5)	0.04323 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0373 (12)	0.0361 (11)	0.0353 (12)	−0.0031 (9)	−0.0045 (9)	−0.0144 (9)
C2	0.0413 (13)	0.0396 (12)	0.0386 (12)	0.0032 (10)	−0.0083 (10)	−0.0183 (10)
C3	0.0338 (12)	0.0343 (11)	0.0356 (12)	−0.0031 (9)	−0.0029 (9)	−0.0140 (9)
C4	0.0367 (12)	0.0366 (11)	0.0330 (11)	−0.0036 (9)	−0.0023 (9)	−0.0143 (9)
C5	0.0407 (13)	0.0376 (12)	0.0418 (13)	0.0040 (9)	−0.0072 (10)	−0.0187 (10)
C6	0.0458 (14)	0.0420 (13)	0.0397 (13)	0.0042 (10)	−0.0096 (10)	−0.0150 (10)
C7	0.0462 (14)	0.0446 (13)	0.0351 (12)	−0.0022 (10)	−0.0070 (10)	−0.0172 (10)
C8	0.0632 (17)	0.0386 (13)	0.0430 (14)	0.0075 (11)	−0.0057 (12)	−0.0201 (11)
C9	0.0591 (16)	0.0364 (12)	0.0367 (13)	0.0072 (11)	−0.0075 (11)	−0.0120 (10)
C10	0.0424 (13)	0.0361 (11)	0.0330 (11)	−0.0059 (9)	−0.0065 (9)	−0.0120 (9)
C11	0.0389 (13)	0.0344 (11)	0.0362 (12)	0.0001 (9)	−0.0082 (9)	−0.0139 (9)
C12	0.0408 (13)	0.0323 (11)	0.0412 (13)	−0.0040 (9)	−0.0083 (10)	−0.0111 (10)
C13	0.0455 (14)	0.0412 (13)	0.0421 (13)	0.0056 (10)	−0.0064 (10)	−0.0151 (11)
C14	0.0469 (14)	0.0403 (12)	0.0401 (13)	0.0065 (10)	−0.0106 (10)	−0.0195 (10)
C15	0.0574 (18)	0.0586 (17)	0.0622 (18)	0.0117 (13)	−0.0036 (13)	−0.0337 (15)
C16	0.0653 (19)	0.0571 (17)	0.0551 (17)	−0.0137 (14)	0.0023 (14)	−0.0169 (14)
Br1	0.0754 (3)	0.0649 (2)	0.0424 (2)	0.01792 (15)	−0.02126 (14)	−0.03068 (15)
N1	0.0399 (11)	0.0354 (10)	0.0337 (10)	−0.0008 (8)	−0.0039 (8)	−0.0148 (8)
N2	0.0436 (11)	0.0422 (10)	0.0354 (10)	0.0031 (8)	−0.0081 (8)	−0.0190 (9)
O1	0.0461 (10)	0.0369 (8)	0.0449 (10)	0.0083 (7)	−0.0082 (7)	−0.0129 (7)
O2	0.0490 (10)	0.0522 (10)	0.0439 (10)	0.0094 (8)	−0.0120 (8)	−0.0266 (8)
O3	0.0600 (11)	0.0429 (9)	0.0409 (10)	0.0003 (8)	−0.0174 (8)	−0.0082 (8)
O4	0.0639 (12)	0.0727 (13)	0.0527 (11)	0.0297 (10)	−0.0291 (10)	−0.0341 (10)
S1	0.0489 (4)	0.0446 (3)	0.0365 (3)	0.0065 (3)	−0.0140 (2)	−0.0173 (3)

Geometric parameters (Å, º)

C1—N1	1.292 (3)	C10—C11	1.370 (3)
C1—N2	1.392 (3)	C10—H10	0.9300
C1—S1	1.728 (2)	C11—C14	1.454 (3)
C2—C3	1.356 (3)	C11—C12	1.457 (3)
C2—S1	1.708 (2)	C12—O3	1.202 (3)
C2—H2	0.9300	C12—O1	1.367 (3)
C3—N1	1.390 (3)	C13—O1	1.437 (3)
C3—C4	1.470 (3)	C13—O2	1.443 (3)
C4—C9	1.396 (3)	C13—C16	1.501 (4)
C4—C5	1.398 (3)	C13—C15	1.509 (3)
C5—C6	1.379 (4)	C14—O4	1.211 (3)
C5—H5	0.9300	C14—O2	1.347 (3)
C6—C7	1.382 (3)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.375 (4)	C15—H15C	0.9600
C7—Br1	1.893 (2)	C16—H16A	0.9600
C8—C9	1.378 (4)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C9—H9	0.9300	N2—H2N	0.8600
C10—N2	1.331 (3)
N1—C1—N2	124.2 (2)	C14—C11—C12	119.7 (2)
N1—C1—S1	116.01 (17)	O3—C12—O1	118.4 (2)
N2—C1—S1	119.74 (17)	O3—C12—C11	126.3 (2)
C3—C2—S1	110.75 (18)	O1—C12—C11	115.3 (2)
C3—C2—H2	124.6	O1—C13—O2	110.1 (2)
S1—C2—H2	124.6	O1—C13—C16	110.2 (2)
C2—C3—N1	115.0 (2)	O2—C13—C16	111.1 (2)
C2—C3—C4	125.4 (2)	O1—C13—C15	106.4 (2)
N1—C3—C4	119.6 (2)	O2—C13—C15	104.8 (2)
C9—C4—C5	118.1 (2)	C16—C13—C15	114.0 (2)
C9—C4—C3	120.5 (2)	O4—C14—O2	118.1 (2)
C5—C4—C3	121.4 (2)	O4—C14—C11	124.9 (2)
C6—C5—C4	121.1 (2)	O2—C14—C11	117.0 (2)
C6—C5—H5	119.5	C13—C15—H15A	109.5
C4—C5—H5	119.5	C13—C15—H15B	109.5
C5—C6—C7	118.9 (2)	H15A—C15—H15B	109.5
C5—C6—H6	120.5	C13—C15—H15C	109.5
C7—C6—H6	120.5	H15A—C15—H15C	109.5
C8—C7—C6	121.6 (2)	H15B—C15—H15C	109.5
C8—C7—Br1	118.11 (19)	C13—C16—H16A	109.5
C6—C7—Br1	120.31 (19)	C13—C16—H16B	109.5
C7—C8—C9	119.1 (2)	H16A—C16—H16B	109.5
C7—C8—H8	120.5	C13—C16—H16C	109.5
C9—C8—H8	120.5	H16A—C16—H16C	109.5
C8—C9—C4	121.2 (2)	H16B—C16—H16C	109.5
C8—C9—H9	119.4	C1—N1—C3	109.7 (2)
C4—C9—H9	119.4	C10—N2—C1	124.2 (2)
N2—C10—C11	124.3 (2)	C10—N2—H2N	117.9
N2—C10—H10	117.9	C1—N2—H2N	117.9
C11—C10—H10	117.9	C12—O1—C13	118.47 (18)
C10—C11—C14	121.0 (2)	C14—O2—C13	117.94 (19)
C10—C11—C12	119.2 (2)	C2—S1—C1	88.54 (11)
S1—C2—C3—N1	−0.8 (3)	C12—C11—C14—O4	163.4 (3)
S1—C2—C3—C4	178.57 (18)	C10—C11—C14—O2	169.8 (2)
C2—C3—C4—C9	−9.0 (4)	C12—C11—C14—O2	−14.2 (3)
N1—C3—C4—C9	170.3 (2)	N2—C1—N1—C3	178.0 (2)
C2—C3—C4—C5	171.0 (2)	S1—C1—N1—C3	−0.2 (3)
N1—C3—C4—C5	−9.6 (3)	C2—C3—N1—C1	0.7 (3)
C9—C4—C5—C6	0.1 (4)	C4—C3—N1—C1	−178.7 (2)
C3—C4—C5—C6	−180.0 (2)	C11—C10—N2—C1	−176.8 (2)
C4—C5—C6—C7	0.2 (4)	N1—C1—N2—C10	−10.6 (4)
C5—C6—C7—C8	−0.2 (4)	S1—C1—N2—C10	167.55 (19)
C5—C6—C7—Br1	178.59 (19)	O3—C12—O1—C13	−163.3 (2)
C6—C7—C8—C9	−0.3 (4)	C11—C12—O1—C13	20.4 (3)
Br1—C7—C8—C9	−179.0 (2)	O2—C13—O1—C12	−50.1 (3)
C7—C8—C9—C4	0.6 (4)	C16—C13—O1—C12	72.8 (3)
C5—C4—C9—C8	−0.5 (4)	C15—C13—O1—C12	−163.1 (2)
C3—C4—C9—C8	179.5 (2)	O4—C14—O2—C13	164.6 (3)
N2—C10—C11—C14	−0.8 (4)	C11—C14—O2—C13	−17.7 (3)
N2—C10—C11—C12	−176.8 (2)	O1—C13—O2—C14	48.4 (3)
C10—C11—C12—O3	12.9 (4)	C16—C13—O2—C14	−73.9 (3)
C14—C11—C12—O3	−163.2 (2)	C15—C13—O2—C14	162.5 (2)
C10—C11—C12—O1	−171.1 (2)	C3—C2—S1—C1	0.51 (19)
C14—C11—C12—O1	12.8 (3)	N1—C1—S1—C2	−0.2 (2)
C10—C11—C14—O4	−12.7 (4)	N2—C1—S1—C2	−178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4	0.86	2.06	2.704 (3)	131